Drag is art, drag is exciting, drag is… old? This week, Maia explores the history of drag. From drag in Ancient Greece and Rome and male only casts, to more contemporary artist like the work of Julian Eltinge. Maia shares the life of William Dorsey Swann, who was America’s first drag queen, or at least one of them. Taking us to the Drag Balls of Harlem during the Harlem Renaissance and the extravagant homes of DC that first held drag gatherings. Swann’s life proves that drag has history in America. Take a swan dive in the life of “William Dorsey Swann”!
Meet the queen who started it all—corset, courage, and all. In this episode, Grant and Maia dive into the incredible true story of William Dorsey Swann, a formerly enslaved man who threw fierce drag balls in 1880s Washington, DC—decades before Stonewall and centuries before RuPaul. Swann didn’t just sashay through history; he kicked down doors, defied police raids, and claimed space for Black queer joy at a time when both his race and gender expression were criminalized. From glitter and grit to protest and pride, this episode uncovers how Swann’s radical legacy echoes through today’s culture wars, including a powerful tribute during the George Floyd protests on the very street that now bears his name. If you love history served with sass, struggle, and seriously good storytelling—this one’s for you.
00:00:00 Catch-Up
00:22:21 Swann Dive
00:39:40 Defining Drag
00:47:20 Forgotten History Uncovered
01:00:00 Queens of Freedom
01:03:30 "Cake Walk"
01:22:36 Activism’s Legal Legacy
01:41:00 Swann Street Redemption
Connect with Us
Love a good laugh? Stay in the loop with the Well, I Laughed Podcast! Hit up wellilaughed.com for all the fun, throw some love our way on Patreon at https://patreon.com/WellILaughedPodcast, and send us your wildest listener stories at wellilaughedpod@gmail.com—because let’s be real, we know you’ve got some!
Listener stories, topic ideas, or anything else you think belongs on the show—drop it all at wellilaughed.com/contact. We’re all ears—and laughs!
Follow Us On Social Media
Instagram: @wellilaughed
Tiktok: @wellilaughed
Facebook: Well, I Laughed Podcast
YouTube: Well, I laughed
